DnDWiki:Diplomacy

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You can change the attitudes of others (nonplayer characters) with a successful Diplomacy check see the Influencing NPC Attitudes sub-section below, for basic DCs. In negotiations, participants roll opposed Diplomacy checks, and the winner gains the advantage. Opposed checks also resolve situations when two advocates or diplomats plead opposite cases in a hearing before a third party.

Optional, but not recommended because retries usually do not work. Even if the initial Diplomacy check succeeds, the other character can be persuaded only so far, and a retry may do more harm than good. If the initial check fails, the other character has probably become more firmly committed to his position, and a retry is futile.